NPASS Compound

Structure

NPC473361 OpenBabel07101718182D 29 29 0 0 1 0 0 0 0 0999 V2000 -1.4076 0.7909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7046 2.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8387 -1.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7779 2.9613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2082 -2.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -3.3047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2742 -0.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5698 -2.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4126 -1.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6343 -2.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6343 2.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7914 1.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2040 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4126 1.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6347 1.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9959 -0.9120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5698 2.0493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7914 -1.6434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7046 -2.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3387 -0.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9959 0.9120 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2082 0.9120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2082 -0.9120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5474 -2.6567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8710 -1.6203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8387 1.3179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6347 -1.3179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8710 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 22 2 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 18 23 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 27 1 1 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 23 28 1 1 0 0 0 24 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.26
Volume:	443.236
LogP:	3.19
LogD:	2.998
LogS:	-4.874
# Rotatable Bonds:	5
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	4.7
Fsp3:	0.583
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	2.5868555894703604e-05
Pgp-inhibitor:	0.045
Pgp-substrate:	0.679
Human Intestinal Absorption (HIA):	0.763
20% Bioavailability (F20%):	0.231
30% Bioavailability (F30%):	0.238

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	97.63489532470703%
Volume Distribution (VD):	1.458
Pgp-substrate:	4.638117790222168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.101
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.657
CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.42
CYP2D6-substrate:	0.07
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	2.073
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.992
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.339
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.133
Carcinogencity:	0.018
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.826

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC473361

Natural Product ID:	NPC473361
*Common Name:**	Gibberosene F
IUPAC Name:	[(1R,2E,6E,8R,10Z,12E,14R)-14-acetyloxy-8-hydroxy-2,6,10-trimethyl-13-propan-2-ylcyclotetradeca-2,6,10,12-tetraen-1-yl] acetate
Synonyms:	gibberosene F
Standard InCHIKey:	SVAFVUMQBHODCP-QLPDOKLOSA-N
Standard InCHI:	InChI=1S/C24H36O5/c1-15(2)22-12-11-17(4)14-21(27)13-16(3)9-8-10-18(5)23(28-19(6)25)24(22)29-20(7)26/h10-13,15,21,23-24,27H,8-9,14H2,1-7H3/b16-13+,17-11-,18-10+,22-12+/t21-,23+,24+/m0/s1
SMILES:	CC1=CC(CC(=CC=C(C(C(C(=CCC1)C)OC(=O)C)OC(=O)C)C(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403025
PubChem CID:	44448180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000008] Cembrane diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921403]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16124762]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16989519]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17917291]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[18198839]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561904]
NPO25026	Sinularia gibberosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523821]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523821]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[523821]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[523821]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC473361 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1309
0.2-0.3	5753
0.3-0.4	17105
0.4-0.5	11033
0.5-0.6	5177
0.6-0.7	1882
0.7-0.8	254
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329904
0.8841	High Similarity	NPC4299
0.8732	High Similarity	NPC315843
0.8732	High Similarity	NPC107654
0.8714	High Similarity	NPC316185
0.8696	High Similarity	NPC101622
0.8649	High Similarity	NPC471537
0.8451	Intermediate Similarity	NPC477086
0.8451	Intermediate Similarity	NPC472254
0.8451	Intermediate Similarity	NPC477087
0.8421	Intermediate Similarity	NPC474894
0.8333	Intermediate Similarity	NPC477085
0.8169	Intermediate Similarity	NPC151481
0.8133	Intermediate Similarity	NPC84360
0.8	Intermediate Similarity	NPC146811
0.8	Intermediate Similarity	NPC301525
0.7973	Intermediate Similarity	NPC470686
0.7949	Intermediate Similarity	NPC315731
0.7941	Intermediate Similarity	NPC55376
0.7922	Intermediate Similarity	NPC86971
0.7901	Intermediate Similarity	NPC61527
0.7895	Intermediate Similarity	NPC315394
0.7895	Intermediate Similarity	NPC40049
0.7887	Intermediate Similarity	NPC193029
0.7887	Intermediate Similarity	NPC473357
0.7875	Intermediate Similarity	NPC161670
0.7857	Intermediate Similarity	NPC282760
0.7846	Intermediate Similarity	NPC329686
0.7808	Intermediate Similarity	NPC476037
0.7808	Intermediate Similarity	NPC59558
0.7805	Intermediate Similarity	NPC45409
0.7792	Intermediate Similarity	NPC474816
0.7792	Intermediate Similarity	NPC209135
0.7778	Intermediate Similarity	NPC273508
0.7778	Intermediate Similarity	NPC471494
0.7778	Intermediate Similarity	NPC209327
0.7778	Intermediate Similarity	NPC310210
0.7763	Intermediate Similarity	NPC469880
0.775	Intermediate Similarity	NPC16488
0.775	Intermediate Similarity	NPC44261
0.775	Intermediate Similarity	NPC161045
0.7722	Intermediate Similarity	NPC184208
0.7722	Intermediate Similarity	NPC112868
0.7722	Intermediate Similarity	NPC8538
0.7692	Intermediate Similarity	NPC477088
0.7683	Intermediate Similarity	NPC311163
0.7683	Intermediate Similarity	NPC315395
0.7683	Intermediate Similarity	NPC316426
0.7662	Intermediate Similarity	NPC262747
0.7654	Intermediate Similarity	NPC186155
0.7654	Intermediate Similarity	NPC78673
0.7654	Intermediate Similarity	NPC160517
0.7654	Intermediate Similarity	NPC475706
0.7647	Intermediate Similarity	NPC222852
0.7639	Intermediate Similarity	NPC478097
0.7639	Intermediate Similarity	NPC478100
0.7625	Intermediate Similarity	NPC474028
0.7625	Intermediate Similarity	NPC474439
0.7606	Intermediate Similarity	NPC96414
0.7606	Intermediate Similarity	NPC19769
0.76	Intermediate Similarity	NPC329890
0.759	Intermediate Similarity	NPC313658
0.759	Intermediate Similarity	NPC316138
0.7568	Intermediate Similarity	NPC476012
0.7564	Intermediate Similarity	NPC279532
0.7561	Intermediate Similarity	NPC474424
0.7561	Intermediate Similarity	NPC35933
0.7561	Intermediate Similarity	NPC11804
0.7534	Intermediate Similarity	NPC474823
0.7534	Intermediate Similarity	NPC238223
0.7532	Intermediate Similarity	NPC477202
0.7531	Intermediate Similarity	NPC23748
0.7531	Intermediate Similarity	NPC49208
0.75	Intermediate Similarity	NPC475944
0.75	Intermediate Similarity	NPC474280
0.75	Intermediate Similarity	NPC478101
0.75	Intermediate Similarity	NPC201356
0.747	Intermediate Similarity	NPC116575
0.7468	Intermediate Similarity	NPC139712
0.7468	Intermediate Similarity	NPC1180
0.7467	Intermediate Similarity	NPC293114
0.7467	Intermediate Similarity	NPC477084
0.7463	Intermediate Similarity	NPC96663
0.7439	Intermediate Similarity	NPC243618
0.7439	Intermediate Similarity	NPC474776
0.7439	Intermediate Similarity	NPC70424
0.7436	Intermediate Similarity	NPC116177
0.7436	Intermediate Similarity	NPC7563
0.7436	Intermediate Similarity	NPC474278
0.7436	Intermediate Similarity	NPC476439
0.7436	Intermediate Similarity	NPC477203
0.7436	Intermediate Similarity	NPC320630
0.7432	Intermediate Similarity	NPC472947
0.7432	Intermediate Similarity	NPC329656
0.7432	Intermediate Similarity	NPC475004
0.7429	Intermediate Similarity	NPC26810
0.7407	Intermediate Similarity	NPC324170
0.7407	Intermediate Similarity	NPC323251
0.7403	Intermediate Similarity	NPC260396
0.7397	Intermediate Similarity	NPC132286
0.7397	Intermediate Similarity	NPC472266
0.7391	Intermediate Similarity	NPC122239
0.7391	Intermediate Similarity	NPC322186
0.7381	Intermediate Similarity	NPC199382
0.7368	Intermediate Similarity	NPC329914
0.7368	Intermediate Similarity	NPC284006
0.7361	Intermediate Similarity	NPC476655
0.7361	Intermediate Similarity	NPC478099
0.7361	Intermediate Similarity	NPC470123
0.7361	Intermediate Similarity	NPC476657
0.7361	Intermediate Similarity	NPC471556
0.7361	Intermediate Similarity	NPC478098
0.7361	Intermediate Similarity	NPC476654
0.7353	Intermediate Similarity	NPC44542
0.7349	Intermediate Similarity	NPC21469
0.7342	Intermediate Similarity	NPC93763
0.7342	Intermediate Similarity	NPC108816
0.7342	Intermediate Similarity	NPC127526
0.7333	Intermediate Similarity	NPC315597
0.7333	Intermediate Similarity	NPC469660
0.7333	Intermediate Similarity	NPC315285
0.7326	Intermediate Similarity	NPC313670
0.7326	Intermediate Similarity	NPC474761
0.7326	Intermediate Similarity	NPC3952
0.7326	Intermediate Similarity	NPC316228
0.7326	Intermediate Similarity	NPC475879
0.7326	Intermediate Similarity	NPC476004
0.7324	Intermediate Similarity	NPC155849
0.7324	Intermediate Similarity	NPC217940
0.7317	Intermediate Similarity	NPC231601
0.7317	Intermediate Similarity	NPC315559
0.7317	Intermediate Similarity	NPC474809
0.7317	Intermediate Similarity	NPC42476
0.7317	Intermediate Similarity	NPC475714
0.7308	Intermediate Similarity	NPC236228
0.7308	Intermediate Similarity	NPC188860
0.7308	Intermediate Similarity	NPC203277
0.7308	Intermediate Similarity	NPC256720
0.7308	Intermediate Similarity	NPC68819
0.7297	Intermediate Similarity	NPC313444
0.7297	Intermediate Similarity	NPC272961
0.7297	Intermediate Similarity	NPC63873
0.7294	Intermediate Similarity	NPC227379
0.7294	Intermediate Similarity	NPC474471
0.7286	Intermediate Similarity	NPC19241
0.7286	Intermediate Similarity	NPC327112
0.7284	Intermediate Similarity	NPC52861
0.7273	Intermediate Similarity	NPC471525
0.7262	Intermediate Similarity	NPC164393
0.726	Intermediate Similarity	NPC476659
0.726	Intermediate Similarity	NPC37382
0.726	Intermediate Similarity	NPC476656
0.725	Intermediate Similarity	NPC475210
0.725	Intermediate Similarity	NPC325869
0.725	Intermediate Similarity	NPC242767
0.725	Intermediate Similarity	NPC99651
0.725	Intermediate Similarity	NPC321728
0.7246	Intermediate Similarity	NPC226848
0.7246	Intermediate Similarity	NPC223679
0.7229	Intermediate Similarity	NPC476804
0.7229	Intermediate Similarity	NPC474865
0.7229	Intermediate Similarity	NPC31086
0.7229	Intermediate Similarity	NPC9868
0.7229	Intermediate Similarity	NPC126518
0.7222	Intermediate Similarity	NPC34883
0.7222	Intermediate Similarity	NPC476658
0.7215	Intermediate Similarity	NPC474818
0.7215	Intermediate Similarity	NPC49302
0.7215	Intermediate Similarity	NPC51809
0.7215	Intermediate Similarity	NPC125365
0.7215	Intermediate Similarity	NPC233071
0.7215	Intermediate Similarity	NPC176329
0.7209	Intermediate Similarity	NPC20946
0.7209	Intermediate Similarity	NPC474032
0.7209	Intermediate Similarity	NPC212598
0.7209	Intermediate Similarity	NPC246028
0.7209	Intermediate Similarity	NPC133450
0.72	Intermediate Similarity	NPC475982
0.72	Intermediate Similarity	NPC239373
0.72	Intermediate Similarity	NPC329989
0.72	Intermediate Similarity	NPC269841
0.7195	Intermediate Similarity	NPC474252
0.7195	Intermediate Similarity	NPC474291
0.7195	Intermediate Similarity	NPC471298
0.7195	Intermediate Similarity	NPC313677
0.7183	Intermediate Similarity	NPC64971
0.7179	Intermediate Similarity	NPC315552
0.7179	Intermediate Similarity	NPC478193
0.7179	Intermediate Similarity	NPC478191
0.7179	Intermediate Similarity	NPC478195
0.7179	Intermediate Similarity	NPC478192
0.7179	Intermediate Similarity	NPC329852
0.7179	Intermediate Similarity	NPC478196
0.7179	Intermediate Similarity	NPC478194
0.7176	Intermediate Similarity	NPC131329
0.7176	Intermediate Similarity	NPC86005
0.7176	Intermediate Similarity	NPC477959
0.7176	Intermediate Similarity	NPC474765
0.7162	Intermediate Similarity	NPC194871
0.7162	Intermediate Similarity	NPC25298

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC473361 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	131
0.1-0.2	1745
0.2-0.3	4022
0.3-0.4	2417
0.4-0.5	654
0.5-0.6	127
0.6-0.7	49
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7529	Intermediate Similarity	NPD7838	Discovery
0.7286	Intermediate Similarity	NPD4246	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7983	Approved
0.7229	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD46	Approved
0.7126	Intermediate Similarity	NPD6698	Approved
0.7123	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7154	Phase 3
0.6986	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5362	Discontinued
0.6854	Remote Similarity	NPD7637	Suspended
0.6778	Remote Similarity	NPD5779	Approved
0.6778	Remote Similarity	NPD5778	Approved
0.6747	Remote Similarity	NPD4819	Approved
0.6747	Remote Similarity	NPD4822	Approved
0.6747	Remote Similarity	NPD4820	Approved
0.6747	Remote Similarity	NPD4821	Approved
0.6716	Remote Similarity	NPD6927	Phase 3
0.6707	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4268	Approved
0.6707	Remote Similarity	NPD4271	Approved
0.6706	Remote Similarity	NPD5331	Approved
0.6706	Remote Similarity	NPD5332	Approved
0.6702	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6632	Remote Similarity	NPD5344	Discontinued
0.6596	Remote Similarity	NPD4225	Approved
0.6588	Remote Similarity	NPD4269	Approved
0.6588	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD7839	Suspended
0.6559	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5785	Approved
0.6548	Remote Similarity	NPD4252	Approved
0.6543	Remote Similarity	NPD8264	Approved
0.6543	Remote Similarity	NPD8039	Approved
0.6528	Remote Similarity	NPD6109	Phase 1
0.6528	Remote Similarity	NPD585	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD368	Approved
0.6477	Remote Similarity	NPD5786	Approved
0.6462	Remote Similarity	NPD4265	Approved
0.6444	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD4251	Approved
0.6404	Remote Similarity	NPD4250	Approved
0.6404	Remote Similarity	NPD7524	Approved
0.6395	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD5363	Approved
0.6322	Remote Similarity	NPD6695	Phase 3
0.631	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6411	Approved
0.6292	Remote Similarity	NPD4249	Approved
0.6279	Remote Similarity	NPD5369	Approved
0.6267	Remote Similarity	NPD4194	Approved
0.6267	Remote Similarity	NPD4193	Approved
0.6267	Remote Similarity	NPD4191	Approved
0.6267	Remote Similarity	NPD4192	Approved
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6435	Approved
0.619	Remote Similarity	NPD4756	Discovery
0.619	Remote Similarity	NPD6925	Approved
0.619	Remote Similarity	NPD5776	Phase 2
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6176	Remote Similarity	NPD4220	Pre-registration
0.6163	Remote Similarity	NPD7514	Phase 3
0.6163	Remote Similarity	NPD7332	Phase 2
0.6136	Remote Similarity	NPD6110	Phase 1
0.6125	Remote Similarity	NPD6923	Approved
0.6125	Remote Similarity	NPD6922	Approved
0.6118	Remote Similarity	NPD7145	Approved
0.6117	Remote Similarity	NPD6371	Approved
0.6111	Remote Similarity	NPD342	Phase 1
0.6104	Remote Similarity	NPD3197	Phase 1
0.6098	Remote Similarity	NPD4732	Discontinued
0.6092	Remote Similarity	NPD6902	Approved
0.6087	Remote Similarity	NPD5370	Suspended
0.6082	Remote Similarity	NPD7638	Approved
0.6075	Remote Similarity	NPD7505	Discontinued
0.6071	Remote Similarity	NPD6933	Approved
0.6058	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD7143	Approved
0.6049	Remote Similarity	NPD7144	Approved
0.6047	Remote Similarity	NPD6929	Approved
0.6044	Remote Similarity	NPD7750	Discontinued
0.6027	Remote Similarity	NPD4219	Approved
0.6024	Remote Similarity	NPD6924	Approved
0.6024	Remote Similarity	NPD6926	Approved
0.6	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD5368	Approved
0.5977	Remote Similarity	NPD6931	Approved
0.5977	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6930	Phase 2
0.5976	Remote Similarity	NPD7150	Approved
0.5976	Remote Similarity	NPD7151	Approved
0.5976	Remote Similarity	NPD7152	Approved
0.5957	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD6686	Approved
0.5914	Remote Similarity	NPD6051	Approved
0.5909	Remote Similarity	NPD6898	Phase 1
0.5905	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6640	Phase 3
0.5867	Remote Similarity	NPD9119	Approved
0.5867	Remote Similarity	NPD69	Approved
0.5856	Remote Similarity	NPD8516	Approved
0.5856	Remote Similarity	NPD8517	Approved
0.5856	Remote Similarity	NPD8515	Approved
0.5856	Remote Similarity	NPD8513	Phase 3
0.5843	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6647	Phase 2
0.5814	Remote Similarity	NPD6932	Approved
0.5797	Remote Similarity	NPD5343	Approved
0.5789	Remote Similarity	NPD7087	Discontinued
0.578	Remote Similarity	NPD7115	Discovery
0.5761	Remote Similarity	NPD6422	Discontinued
0.5735	Remote Similarity	NPD39	Approved
0.5733	Remote Similarity	NPD9118	Approved
0.5729	Remote Similarity	NPD6399	Phase 3
0.5682	Remote Similarity	NPD6683	Phase 2
0.5652	Remote Similarity	NPD8273	Phase 1
0.5652	Remote Similarity	NPD6893	Approved
0.5618	Remote Similarity	NPD7509	Discontinued
0.5603	Remote Similarity	NPD8074	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data